Filemail
Send Large Files Of Any Size
Leading product design across a B2B SaaS file-transfer ecosystem — and turning -1.6% YoY paid growth into +19.7%.
Client
Competitors
My Role
Lead Product Designer — UX direction, system design, cross- platform product
Industry
B2B SaaS · File transfer ·Productivity
Deliverables
Site + Strapi component system, desktop product UX, iOS app, Outlook plugin, security UX, marketing system
Filemail is a B2B SaaS file-transfer product competing with WeTransfer, TransferNow, Dropbox, and Massive.io When I joined as Lead Product Designer, paid licenses were trending -1.6% year-to-date. By October 2025, they were up +19.7% YTD, trial-to-paid conversion had climbed from 39% to 53%, and monthly transfer volume had grown from 390k to 500k.
The brief wasn’t a redesign – it was a full system rebuild. New site, new desktop product UX, new iOS app, new Outlook plugin, new transfer-security model, and a Strapi-integrated design system that lets the engineering team ship pages without a designer in the loop. Everything had to work as one product across surfaces and one motion across teams.
Keywords:
– B2B SaaS
– Lead Product Designer
– Multi-platform product
– Design system in Strapi
– Cross-platform UX
– LLM-assisted design
– System-level thinking
– Mentoring & process
The challenge
A mature product with a flat growth curve, a fragmented surface area (web + desktop + mobile + plugin marketing), and a small team that needed to ship more without growing. The work had to land three things at once: a system that compressed the cost of every new page, a product UX that lifted conversion at every funnel step, and a way of working with engineering that didn’t require a designer to be in every decision.
My Role
I lead UX and product direction end-to-end across the full Filemail ecosystem – site, desktop app, iOS, Outlook plugin, transfer security, marketing materials – partnering with engineering, product, and marketing, and using LLM tools throughout discovery and exploration to move faster on the right ideas.
– Lead the UX and product direction across the entire Filemail surface – site, desktop, iOS, Outlook plugin, and marketing system.
– Rebuilt the marketing site and built a component library directly inside Strapi – cutting the time to ship a new page by ~10×, with engineering generating pages without a designer in the loop.
– Redesigned the desktop product end-to-end: New Transfer, Ongoing Transfers, Dashboard, Onboarding, Payment, and Download – improving UX at every funnel step.
– Re-architected the Settings page so users can find and change what they need in seconds – a long-standing complaint point now closed.
– Designed and shipped the iOS mobile app and the Outlook plugin – extending the product beyond desktop and into the user’s actual workflow.
– Defined the transfer-security UX (E2EE and password-protected transfers) – making strong security the default without adding friction.
– Established a comprehensive design system and component library that lets engineering self-serve new pages – reducing design-team load and increasing shipping velocity.
– Produced marketing materials, email templates, and the investor pitch video – keeping product and marketing on one visual system.
– Ran competitive research across WeTransfer, TransferNow, Dropbox, and Massive.io to position Filemail against the category leaders.
– Used LLM tools actively in research and design exploration – for pattern analysis, competitive synthesis, and option generation – to find better design solutions faster.
– Drove alignment between design decisions and the business outcomes that mattered to management (paid licenses, conversion rate, trial signups).
Impact
“Growth doesn’t come from a redesign – it comes from a system. When the same component library powers every page on the site and every screen in the product, every team gets faster, and the user gets one product instead of five.”
Key Screens
Desktop product – core flows
- New Transfer – simplified, faster send
- Ongoing Transfers – clear state and progress
- Dashboard – unified at-a-glance overview
- Onboarding – improved time-to-first-transfer
- Payment – frictionless upgrade flow
- Download Page – focused, conversion-tuned
Goal: Improve UX at every step of the funnel
Security & multi-platform
- E2EE and password-protected transfers
- iOS app – send and manage from mobile
- Outlook plugin – send from inside email
- Settings – re-architected for fast lookup
Goal: Extend the product to where the user actually works – securely.
Process
Discovery & competitive research
Audited WeTransfer, TransferNow, Dropbox, and Massive.io to understand where Filemail could differentiate (security defaults, transfer reliability, multi-platform). Ran user interviews and used LLM tools to accelerate pattern analysis and option generation – turning weeks of synthesis into days.
System architecture (Strapi-integrated design system)
Built a component library directly inside Strapi so marketing pages compose from the same primitives the product is built on. New pages went from a multi-day design + dev loop to engineering self-service – roughly a 10× speedup in page generation, and the marketing site now stays consistent without governance overhead.
Desktop product UX rebuild
Redesigned every step of the funnel: New Transfer, Ongoing Transfers, Dashboard, Onboarding, Payment, Download. The metrics changed in lockstep: conversion from 39% to 53%, trial signups roughly doubling, paid licenses moving from -1.6% YTD into double-digit YTD growth.
Settings re-architecture
The Settings page was rebuilt from the user’s task model, not the back-end structure. Users now find what they need in seconds. This was the small fix that closed a long-standing complaint thread.
Multi-platform extension
Shipped the iOS app and the Outlook plugin – extending Filemail into the user’s actual workflow rather than asking them to switch apps. The Outlook plugin in particular targets the B2B sender behaviour the product is built for.
Security UX
Designed the E2EE and password-protected transfer flows so the secure path is the obvious one – strong security as the default, not a setting you have to hunt for.
Marketing & investor system
Produced email templates, marketing assets, and the investor pitch video on the same visual system – so product, site, and pitch all reinforce each other.
Mentoring & process
Established the patterns and rituals that let the team self-serve: component handoff in Figma, Strapi component documentation, and a design-review cadence that scales without bottlenecking on a single designer.
Outcome & Reflection
Management highlighted that active customers and trial-to-paid conversion were moving in the right direction – validating the product, UX, and system-level changes across the platform. Over the course of the engagement, paid license growth shifted from decline into strong positive growth, trial-to-paid conversion increased from 39% to 53%, trial signups nearly doubled, and monthly transfer volume grew significantly alongside overall platform usage and data throughput.
The story of this project is the story I want to keep telling: a system replaces a backlog. Once design, product, and marketing are wired into the same component library, the work compounds – every page is faster, every product surface stays in step, and the team can ship without waiting on a designer. That’s what makes a B2B SaaS turnaround stick.
